Boston for couples: the most romantic things to do

This go-to guide offers the 12 most romantic things that will make your city stay special, from sunset sailing trips to vineyard tours

Heading to Boston for a long-overdue romantic getaway? This historic American city has plenty of activities for couples. Whether you're thinking about anniversary ideas or searching for the perfect spot to propose, there are plenty of suitable venues in this city.

Looking for fun-filled couples activities? Discover some of Boston's hidden gems so you can avoid the usual crowds. If you want to party into the early hours, Boston's nightlife and bars won't disappoint. If you're still in search of inspiration, read on for a shortlist of 12 romantic things to do in Boston.


1. Set sail from Rowes Wharf to watch the sunset over Boston Harbor

Few areas of the city are as romantic as Boston Harbour. With a Harbor Champagne Sunset Sail, you can admire Boston from the water as you meander through the Harbor Islands and past iconic landmarks like the Boston Fish Pier.

Best time to go:

Boston always looks its best after hours, but nothing beats a hazy sunset on a late summer evening. If you are visiting in winter, bring an extra layer so nothing keeps you from those unmissable views.


2. Jump aboard a trolley together to visit Boston's iconic landmarks

If your feet can't take another hike across the city, a Summer Nights Sunset Trolley Tour is in order. Your guide will regale you with stories about Boston's past as you travel past famous landmarks like Boston Public Garden and zip through districts like Cambridge and Boston's North End.

Best time to go:

While Boston's summertime temperatures are balmy enough, the mercury often falls below freezing in the winter months. If you're visiting in December, you'll definitely want to have your knitwear with you.


3. Share a toast to Boston's famous brews on a VIP brewery tour

If you're looking for low-key date ideas, why not treat yourself to a Guided Craft Brewery Tour? You'll explore four of Boston's best cider houses and breweries, learning about the history of each one as you sample some of the most delicious artisan beers around.

Best time to go:

Boston's breweries tend to get busier during the mid-afternoon. If you want to beat the crowds, think about starting a brewery tour earlier in the day.


4. Enjoy a couple's meal with some of Boston's best-kept culinary secrets

If you think you know everything about the Boston food scene, think again. With a Secret Food Tour, you'll be introduced to less familiar local dishes in Boston's North End, with a local guide on hand to provide you with fascinating insights as you eat.

Best time to go:

Boston's Little Italy is home to some of the most popular attractions in the city. If you're visiting on the weekend, be to contend with crowds of visitors and locals alike.


5. Experience some serious house envy with a Newport mansions tour

Newport, Rhode Island, is often considered America's original resort destination. Today, it's a throwback to the glorious gilded age. With a Newport Mansions Full-Day Trip, the two of you can explore some of the most stunning houses in North America, the Elms and Breakers mansions.

Best time to go:

While the weather is fine during the summer months, you might need to bring an extra layer to keep the chill at bay if you're visiting to take in the sights of New England during the fall.


6. Enjoy a couple's walk among New England's fall foliage

New England is famous for many things, but when autumn rolls around, it's the changing leaves that bring in the crowds. With a Fall Foliage Tour, you'll venture into the White Mountains to see some of the most stunning scenic landscapes in this part of the United States.

Best time to go:

Although it can change from year to year, fall tends to peak between late September and October. If you don't want to miss out on the most breathtaking colors and photo opportunities, try and schedule your trip around then.


7. Spend an evening sipping on artisan beers in some of Boston's oldest taverns

Looking for a light-hearted way to spend an evening with your other half? With a Historic Taverns Tour, you can be both cultured and inebriated at the same time. Tour some of Boston's most long-standing taverns, then jump on a ferry across the Boston Harbor.

Best time to go:

If you want to enjoy the city as you journey between watering holes, try to schedule your trip for early September. This way, you'll beat the leaf chasers and avoid the usual summertime crowds.


8. Grab front-row seats at the Boch Center Wang Theater

If you want to take in some culture during your stay, a Boch Center Wang Theater Behind the Scenes Tour is a must. This legendary live performance venue is a beloved part of Boston's arts scene and boasts one of the biggest stages in America.

Best time to go:

While you can join a tour of this theater any time of the year, you'll want to check the billing to find out which stars are performing if you want to take a seat in the audience.


9. Follow in the footsteps of silver screen couples with a film tour

Boston's been a popular filming location for decades. With a Movie Mile Walking Tour, you'll see where some of the most celebrated films and television shows of all time were shot. You'll even stop at the original location for the legendary sitcom Cheers.

Best time to go:

Boston's most iconic locations aren't going anywhere, but you'll do well to avoid the high season. Generally speaking, spring and autumn are the busiest in Boston.


10. Escape to Martha's Vineyard for a romantic island day out

While you'll never tire of romantic things to do in Boston, sometimes it pays to look further afield. With a Martha's Vineyard Day Trip, you'll depart by ferry to one of New England's most enchanting islands. You can opt for a guided tour or choose to explore at your own pace.

Best time to go:

The island is popular with visitors during summer, but it also comes alive during the fall season. If you're not a fan of crowds, you might want to consider visiting in the spring.


11. Get a taste for the glitz at Boston's most affluent neighborhoods

Back Bay has long been considered one of Boston's most luxurious districts. Today, it's a treasure trove of designer boutiques, art galleries, and restaurants. In other words, it's perfect for date night. With a Back Bay History and Culture Private Walking Tour, you'll find plenty of inspiration for a romantic evening.

Best time to go:

Back Bay's cultural attractions draw in the crowds throughout the week, but you'll find things get a little busier during the weekend.


12. Take your time strolling Boston's Freedom Trail hand in hand

Prefer to go at your own pace? With Boston History and Highlights Self-Guided Audio Tour, you can stroll along the Freedom Trail and marvel at some of the city's most historic landmarks. You can spend as long as you want at each attraction or make as many detours as you wish.

Best time to go:

The great thing about a self-guided tour is you can set your own pace. If the lines look too busy at one destination, simply move on to the next stop on your list.


What are some of the most romantic activities to do in Boston?

You'll find plenty of ideas for date nights in Boston. Enjoy a romantic stroll along the Boston Harborwalk or take to the water with a sunset cruise. Whether you're visiting for the weekend or staying in town longer, there's plenty to keep couples entertained here.

What are some offbeat things to do in Boston?

If romantic dinners for two aren't your thing, why not brave a late-night ghost tour through some of Boston's most haunted districts? Visit the graves of long-dead Bostonians and feel your spine tingle as you explore historic cemeteries and burial grounds.

What are the most romantic spots to watch the sunset in Boston?

Boston Harbor is one of the most romantic spots in the entire city. Enjoy it from the shore or climb aboard a charter cruise to explore the Inner Harbor Islands. Alternatively, head to the North End district. Boston's very own Little Italy isn't short on quaint restaurants that are the perfect place for candlelit dinners and lazy brunches.

What are some romantic day trips from Boston?

If you want to explore beyond Boston, there are many day trip destinations to consider. Head to Martha's Vineyard, Cape Cod, or Provincetown. If you're a self-proclaimed city dweller, you can even visit New York within a day.

What are the best places to take romantic photos in Boston?

Looking to fill your camera roll with romantic snaps during your stay in Boston? Head to the Charles River Esplanade, Beacon Hill, or Boston Public Garden. If you're heading offshore, Castle Island will serve as a brilliant backdrop for your vacation photos.